156575-59-6

Upstream product

• 100-42-5 styrene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 536-74-3 phenylacetylene 
• 72035-41-7 2-methoxybenzo[d][1,3,2]dioxaborole 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 17376-04-4 2-phenethyl iodide 
• 24182-83-0 (E)-styryl(p-tolyl)sulfane 

Downstream Products

• 60-12-8 2-phenylethanol 
• 112947-62-3 3-phenyl-1-(trimethylsilyl)propan-1-ol 
• 122-97-4 3-Phenyl-1-propanol 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 71747-37-0 (S)-1-phenylpentan-3-ol 
• 105836-17-7 (R)-1-phenyl-3-pentanol 
• 1142-22-9 (E)-1,4-diphenylbut-2-ene 
• 17486-86-1 1,5-diphenylpentan-3-ol 
• 935662-26-3 (R)-2-(2-benzyl-4-phenyl-1-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 935662-22-9 (S)-2-(2-benzyl-4-phenyl-1-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 935662-30-9 (R)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 935662-21-8 (S)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Gold(0) nanoparticles for selective catalytic diboration

Going with gold: Gold(0) nanoparticles stabilized with the diphosphine ligand binap mediate the catalytic diboration of styrene, resulting in complete formation of the bis(boronate)ester product. The gold(0) catalytic mechanism can involve base-assisted h

Light-Mediated Sulfur-Boron Exchange

Interaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters is described. The reaction is promoted by an organic photocatalyst (3DPA2FBN) u

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Hydroboration of Alkenes Catalysed by a Nickel N-Heterocyclic Carbene Complex: Reaction and Mechanistic Aspects

The pentamethylcyclopentadienyl N-heterocyclic carbene nickel complex [Ni(η5-C5Me5)Cl(IMes)] (IMes=1,3-dimesitylimidazol-2-ylidene) efficiently catalyses the anti-Markovnikov hydroboration of alkenes with catecholborane in

Metal-Free Radical Borylation of Alkyl and Aryl Iodides

A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed.

Imido-hydrido complexes of Mo(IV): Catalysis and mechanistic aspects of hydroboration reactions

Imido-hydrido complexes (ArN)Mo(H)(Cl)(PMe3)3 (1) and (ArN)Mo(H)2(PMe3)3 (2) (Ar = 2,6-diisopropylphenyl) catalyse a variety of hydroboration reactions, including the rare examples of addition of HBCat to nitriles to form bis(borylated) amines RCH2N(BCat)2. Stoichiometric reactivity of complexes 1 and 2 with nitriles and HBCat suggest that catalytic reactions proceed via a series of agostic borylamido and borylamino complexes. For complex 1, catalysis starts with addition of nitriles across the Mo-H bond to give (ArN)Mo(Cl)(NCHR)(PMe3)2; whereas for complex 2 stoichiometric reactions suggest initial addition of HBCat to form the agostic complex Mo(H)2(PMe3)3(η3-NAr-HBcat) (16).

Catalytic hydroboration by an imido-hydrido complex of Mo(iv)

The imido-hydrido complex (ArN)Mo(H)(Cl)(PMe3)3 catalyses a variety of hydroboration reactions, including the first example of catalytic addition of HBCat to nitriles to form the bis(borylated) amines RCH2N(BCat)2/su

Synthesis of group 9 metal-olefin complexes with identical ligand frameworks and comparison of their catalytic activity in [2+2+2] cycloaddition and other addition reactions

The preparation and catalytic evaluation of the three group 9 (cyclopentadienyl)metal(trimethylvinylsilane) complexes of the type C 5H5M(H2C=CHSiMe3)2 (M=cobalt, rhodium and iridium) are reported. The complexes were investigated in [2+2+2] cycloaddition as well as in hydrogenation, hydroformylation and hydroboration reactions. Despite the identical organic frameworks and structural parameters, the complexes display remarkable reactivity and stability differences. Copyright

Electronic tuning of a carbene center via remote chemical induction, and relevant effects in catalysis

The present report develops the idea that an N-heterocyclic carbene incorporating a remote anionic functionality-here, a malonate group-as a backbone component of its heterocy- clic framework, can be post-function- alized directly from its transition- metal complexes, upon simple addition of a variety of electrophiles interacting directly with the malonate group in the outer coordination sphere. From a palette of selected electrophilic reagents, it was thus possible to modulate the electronic donor properties of the car- bene center over a rather broad range. Both the zwitterionic complex [Rh{malo-NHCj(cod)] and the cationic derivatives [Rh{malo-NHCE}(cod)] + (where ma/o-NHCE represents the ligand modified by a selected electro- phile E ) were used as pre-catalysts in two types of catalytic reactions, namely, the polymerization of phenyl- acetylene and the hydroboration of styrene. The results indicate that, in both cases, the zwitterionic species is by far the best catalyst, whereas a decrease in the ligand donicity induced by the added electrophile results in a concomitant reduction of catalytic activity. Apparent deviations to such a trend in the case of the hydroboration of styrene were rationalized in terms of an interaction between the reactive catechol- borane substrate and the remote functionality of the N-heterocyclic carbene leading to an in situ modification of the nature of the active species. These observations serve as a useful basis to define the scope and limitations of the present conceptual approach in catalysis.

Chemoselective hydroboration of alkynes vs. alkenes over gold catalysts

Alkynes are preferentially hydroborated in the presence of alkenes when using gold catalysts; the active species involves a borane-gold interaction.